Create + Cultivate

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‘Real Stories’ From Vistaprint Alum: Mary Orton, Entrepreneur, Investor and Influencer

As part of our Create & Cultivate x Vistaprint Brand Campus, we’re sharing all the ways that Vistaprint can help you grow, adapt, and evolve your business. Explore ‘Real Stories’ from Vistaprint Alums, and learn how entrepreneurs use Vistaprint as a one-stop-shop for all of their small business marketing solutions.

Whether you’re sourcing a physical product, seeking digital design services, or simply looking for inspiration, Vistaprint is the marketing partner that enables small business owners to elevate their brands – at every stage of their journey. Read on to discover how real business owners use Vistaprint's design capabilities and wide product selection to help their businesses grow organically—and how you can too.

Mary Orton, Founder, Owning the Interview and Memorandum

What do you love most about having your own brand/ business?

Between my husband and I, we run several businesses and find entrepreneurship to be both incredibly challenging and hugely rewarding. Controlling your own schedule and having the independence to build a business you’re passionate about makes the grueling hours entirely worthwhile. I’m also an unusual mix of right and left brain, so I love that entrepreneurship often provides opportunities to use both business analytical skills as well as creative skills. As someone who started her career on Wall Street, I know that I would not be personally fulfilled by a job that only allows me to utilize one side of my brain!

Have you always been entrepreneurial? What led you to take that first step and establish your own brand/business?Yes, I’ve definitely always had the entrepreneurial bug. In addition to Owning The Interview, Memorandum, and our other businesses, my husband and I are angel investors and are constantly talking about new, disruptive businesses and industries. Even when we were fresh out of college and both working for large investment banks, we were constantly discussing business ideas.

In many cases, I think the best businesses arise from a challenge you’ve experienced firsthand. Our most recent endeavor which is our digital interview course, Owning The Interview, was born out of our personal experience on both sides of the interview table and our realization that there was a huge hole in the market. We’ve seen repeatedly that even the most qualified candidates are often overcome by nerves, stumbling over the smallest details in the interview process. Yet, no one was providing people with comprehensive interview training that went beyond the superficial “sit up straight and make eye contact” and really dug into the strategies and psychology that make a candidate stand out. We decided to take our combined 30 years of experience on both sides of the interview table, along with insights from dozens of executives and hiring managers from Fortune 500 companies, startups and everything in between to create a comprehensive, universal interview course that provides the real insider tips to approach any interview with complete confidence.

What challenges have you faced in launching your brand / business? How did you overcome them?

I think one of my biggest professional faults is the tendency to be a perfectionist. I’ve learned over the years that when you’re starting a new business, the desire to work on something until it’s “perfect” is often counterproductive. It’s more important to get your product (or service) out in the market, solidify product-market fit, and get customer feedback.

For example, we began working on Owning The Interview almost two years ago and in early March of 2020 we were solidifying a production studio in NYC to help us film all of the course videos and content. Days later, Covid hit and we have spent the entire pandemic at our home in Wisconsin. While it was far from ideal, we had to adjust our plans for the perfect studio setup and professional film crew and create a makeshift studio at home during quarantine, filming everything ourselves. In the end, it worked out beautifully. Maybe our set design isn’t as perfect as it could have been had we filmed in a professional studio in NYC, but our course sales and feedback speak for itself, surpassing our wildest hopes. People have found immense value in the content and the rest just didn’t really matter. Ideally, style and substance go hand-in-hand, but when it comes down to it and you’re pressed against a wall in a pandemic, substance over style wins everytime!

How has Vistaprint helped you grow, evolve, or adapt your business? What are some of the tools and services you have used and how did they help you? 

Vistaprint has long been our go-to for marketing materials, branded merch for our team or personalized items to send to business partners. Whether it’s business cards, t-shirts or even fun items like mugs and water bottles, we know we can always rely on the quality of Vistaprint products.

How do visual elements play a role in your branding? How are they important to your overall marketing strategy?

A strong visual brand is hugely important for any business. It engenders trust in the company, makes your business memorable, facilitates referrals and so much more. Especially in the digital age, visual branding that is weak or inconsistent can significantly undermine your credibility, no matter how spectacular your product or service. Strong visual elements, executed consistently wherever your business is represented, can be one of the best ways to communicate with current and prospective customers.

What tips would you give to other aspiring female entrepreneurs to help them launch or scale their businesses?

You have to be willing to roll up your sleeves and tackle anything that comes your way. No task is too small and no job is beneath you. For example, when I was starting out, I knew nothing about how to create a website and didn’t have the budget to hire a web developer. There also weren’t nearly the same resources online for creating inexpensive, visually-appealing websites as there are today. Instead, I had to spend many late nights researching HTML coding and figuring out how to take a basic wordpress template and make it my own. Would I have preferred to focus all of my energy on the big-picture tasks in building the business? Of course. But especially when starting out, you have to be creative and as the saying goes, there’s no substitute for hard work. Entrepreneurship is not glamorous, despite what social media might make you think!

What would you like to see change for the next generation of female entrepreneurs?

As investors, my husband and I are particularly interested in helping underrepresented founders and this certainly includes female entrepreneurs. Throughout my career, I’ve been in countless meetings where investors ask me questions that they would never ask my husband or other white male business partners. The biases that exist result in female and BIPOC founders receiving disproportionately less funding to start businesses. I certainly hope to see this change for the next generation of entrepreneurs.


Mary Orton is an entrepreneur, investor, and the influencer behind fashion and lifestyle blog, Memorandum. In late 2020, she launched Owning The Interview, the premier online interview course helping every job seeker learn the insider tips to land their dream job. Before starting her own businesses, Mary worked for many years in investment banking in NYC and is a graduate of Georgetown University.


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